Anna Taggaro was a junior at Tree Hill High School who left her boarding school after rumors concerning her sexuality were circulated. She initially grew close to Lucas Scott, whom she was date briefly during the second season, and he was the first person she told about her bisexuality. She would eventually come to terms with her sexuality, telling her parents and confronting her homophobic brother Felix before returning to her boarding school for her senior year.

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Daniella Alonso portrays Anna Taggaro. The character is credited by AfterEllen as the first recurring bisexual character of color on television. Anna moves to Tree Hill to escape rumors that she has been having a relationship with another girl. She is first introduced in season two’s "I Will Dare", when she helps Lucas escape the security guards at the local mall. The two then go to a pizzeria together. She and Lucas watch a meteor shower which her brother Felix disapproves of. They decide to take things slow becoming ‘friends with potential’, however she offers him sex after a formal dance, which he turns down due to not being in love with her. Lucas ends the relationship after realizing that he has feelings for Brooke, however the two remain friends as she confides her sexuality to him. Anna forms a strong relationship with Peyton and kisses her after misreading the signs. When she discovers that Felix wrote ‘dyke’ on Peyton’s locker she turns him in getting him expelled. She comes out to him and states how hurt she is by his use of the word. Anna decides that she should stop running from who she is and comes out to her parents, and eventually leaves Tree Hill to re-join her previous school.

When creating characters for the second season, Mark Schwahn had wanted to add a family, which the addition of Anna and Felix allowed him to do. Once casting Daniella Alonso, he refrained from telling her that the rumors were true, however once informing her on her character’s back story it was like “flipping a switch” as she knew what to play. The character was made bisexual as opposed to a lesbian so that her past could be kept secret. Anna was presented as a romantic interest for Lucas, "[Schwahn] thought if she was strictly a lesbian character, that would be really out of nature for her, and a little disingenuous to lesbians," and they needed to hide what her journey was going to be. Alonso feels that the audience was not receptive to the character initially—especially with a large portion of the audience wanting Brooke and Lucas to be together—however over the course of her arc they began to accept Anna.

"Her use of the word 'gay' instead of 'bisexual' wasn't meant to imply that Anna is not bisexual. If I had known the word bisexual was more taboo, we may have gone in that direction. For me, it seemed like Felix was so homophobic, that for her to say 'I’m gay' to him felt even stronger for her."

— Mark Schwahn on the decision for the character to come out using the word 'gay'.